Charlize Theron – How to fuck a virgin?

My new boyfriend is unexpectedly a virgin, and I need a bit of advice.

Hi

I need some advice.

I’m 28F, my new partner is 25M. We’ve been together a few weeks after being friends a few months. All is good on the relationship side.

Last weekend he let me know that he is a virgin. Sure, cool, no problem, everyone has a first time: helps explain why we never ended up having sex after dates. He also let me know that he has massive anxiety around intercourse and sexual activity in general, exacerbated by the fact that his previous girlfriend was incredibly pushy and resentful about this and basically made it worse by trying to guilt him into sex despite him telling her he wasn’t ready. Uh, hm, okay, that’s less straightforward.

He’ll happily touch me and has very happily offered to go down on me, which he’s done before with his ex and enjoyed.

He’s comfy with me playing with his dick (which we’ve done a bit of) and does easily get hard when we mess around. He’s generally very comfy with nudity and touching and kissing (although he does come across very inexperienced… Last night I got to introducing him to kissing with tongues). He’s expressed that he does want sex, and quite happily initiaties foreplay and touching, but seems to become paralysed with anxiety and “stalls” if it seems like actual penetration is going to be expected.

Right now, all I’ve told him is that he can set the pace and we’ll work up to it, he can tell me what he’s not comfortable with. I’ve also told him that, full stop, I’m not going to initiate or expect intercourse unless he explicitly tells me he wants to. We are a foreplay only zone for the time being.

What else can I do here? I genuinely want to help him (I also genuinely want to fuck him), but I’m really not sure what’s the right action to take. I’m privately also a bit worried about whether we’re going to be sexually compatible going forward. We were cuddled in bed chatting about sex, and he was visibly shocked and went very quiet when I mentioned that I’ve done anal (he brought it up).

I’m hoping he’s just a bit sheltered and inexperienced and will open up with time and coaxing, but I honestly have no clue.

What do you think, Reddit?

_____

intotheIR: What you’re doing is exactly right, but he will eventually need a nudge to get the proceedings going (I was once exactly stuck in his situation).

My advice would be to keep going slowly and eventually introduce some dry humping then some nude genitals just touching while grinding together. Eventually, he’s going to get past his anxiety and slide it in.

Being patient and understanding is completely what is called for and you’re doing great.

canon12: Lucky, lucky guy. You guys are going to have a real good time thanks to you, your understanding and patience with him. He will never forget you! The journey is always the most fun part of a relationship. Enjoy!

ourbluntopinion: Great job. Keep doing that, maybe tease him and make sexy stuf seem like a fun game rather than a serious thing so he can be relaxed.

As far as sexual compatibility you can probably teach him what you like and he’ll probably start to like it too

umlaute: Did he tell you why he’s scared of having sex? I was a virgin at 24 and definitly worried about having sex for the first time because it came with so many expectations and so much pressure. Will I get hard? Will I last long enough? Will I last too long? Will it be big enough? Will I be able to satisfy her? Will she still be interested in me if I fail? Will I embarass myself? Will she hurt me (through some comment)?

There’s a lot of stuff going through your head that can easily make you freeze and shut down. Personally, I wouldn’t have had the courage to ask for sex and I didn’t. One evening my girlfriend straight up asked if she’d get to fuck me and I didn’t want to let her down. If she had only waited for me, we probably still wouldn’t have had sexto this day.

I’d try to have a conversation with him about what’s holding him back and what he’s scared of. And then work on solving that together.

randomHiddenQs: > I’m hoping he’s just a bit sheltered and inexperienced and will open up with time and coaxing, but I honestly have no clue.

In all honesty, it sounds like he experienced some sexual trauma in his past. The numbers are 1 in 4 girls and 1 in 6 boys, and based on his reactions and hesitations I would guess that he had an unfortunate past. If so, his reaction to the anal may relate to traumas of his own.

Speaking as a man who had a childhood with sexual traumas, including being raped by an older woman when I was 11, I would say what you are doing sounds exactly like what would be needed for him to feel comfortable. But it’s an internal fight he has to overcome at his own pace.

adaava: If he’s anxious specifically about penetration, but okay with nudity and foreplay, what about you grinding on his dick? I’m not suggesting you do this in order to surprise him with penetration, but just as a middle point between oral/manual foreplay and PIV sex. It might help him get used to, you know, your genitals touching. Ask him if he’d like it and be clear that you won’t turn it into sex and aren’t trying to pressure him, just that it would feel good for both of you.

FiddleWithIt: I think if you like this guy, you will deal with his inexperience and enjoy it as part of who he is. Insecurities and all. Enjoy it. Not everyone in the world eats ass on the regular and I think we are all better off for that.

t1gerfish: I wouldn’t press the issue. Like he said he resented his ex girlfriend for it. I think you guys are going to keep hooking up and he’s going to initiate it most likely. I mean it can get frustrating to have something off limits. Maybe there’s something he wants in order to have sex that would make him feel more safe and responsible about it. I can think of… being scared to ask if you’re on contraception, religious upbringing, maybe he wants to get tested together, maybe he feels like he needs to be sure about you before he does it. Idk people do strange things for all kinds of different reasons…

Yeah, clearly you won’t get to determine sexual compatibility at this time, but there are so many more levels of compatibility that it takes for a relationship to work that you can look into right now. Also, like… I mean… he’s a virgin so you’re probably not going to get your mind blown any time soon.

Dominant_Genes: I’d be PSYCHED to help teach him how to be sexually compatible with you!! That’s the beauty of virgins, teacher and master.

Honestly, I think you need to be a complete adult about this and this weekend tell him in order for sex to work between you, there needs to be communication. That having good sex means talking about it, and that you’ve noticed talking about it seems to make him feel uncomfortable and want to understand why. I’d also reassure him that sex in real life isn’t like porn and you don’t have some pleasure expectations (for now, you can privately have these considerations to share later) but that getting to know one another’s bodies and experimenting with one another is what you’re enjoying most.

Without knowing his history, turn ons, fears and other information you won’t achieve true trust and as a result real intimacy. That may be what he’s been lacking and where his fear or other issues originate from.

Another person wrote recently about how to encourage your partner who has erectile issues during sex. Using language with slight word changes to take the pressure off.

Have you had an orgasm with him yet? Maybe masterbating with his help and making him feel like he’s getting you there will boost his confidence.

All in all being a patient teacher is what is going to work best with him, good luck!

_why_do_U_ask: I have a feeling he may have a problem I had and it is PE. I was able to solve the problem, prior to doing so I was parallelized when dating. So as we got close to having sex I would stop, which sounds like where he maybe at now. The older he is the worse it gets, fear of having PIV and only last 15-30 seconds is a major problem for a male.

The fist time I almost had intercourse I misfired on her legs and she giggled and did not help my over all feeling. She was more experienced than myself. I was luck a divorced mature woman in our neighborhood helped me get over my problem. We did several things over time to help me last longer. It was a memorable summer till she got serious with a mature man and we stopped our sex.

If you let him know you will be comfortable and understanding if he wants intercourse. Fib maybe about a prior BF who had a PE issue that all worked out well once you had sex with him. Or what ever you feel is helpful to calm his concerns. Some men are concerned about their size, assure him you like his manhood.

I still see the women who deflowered me and she always smiles. She said at the end she had taught me well and said I was a good lover. I had already enjoy oral sex, and learned a lot from that point on to ensure lovers would always be satisfied. When you mentioned he does oral, that triggered my memories of why I learned oral and still love it today.

CandyRain_01: OP, my advice to you is to keep doing what you’re doing. Let him move at his pace, but also keep dropping subtle hints that you *want* to teach him, and you *want* to have sex with him regardless of his anxiety. One thing my girlfriend reassured me of is that in order to get good at sex, you have to have it a lot, and it couldn’t be more true. He won’t ever get good and comfortable in bed until he practices. And there’s nothing more comforting than a girl that is understanding and patient and willing to not only teach what she knows, but learn new things as well.

In my opinion, the biggest hurdle for a virgin to get over is admitting it to someone they truly care about. He did that with you, so it’s only a matter of time before he warms up to you further. And trust me, his sex drive will catch up to yours. He just doesn’t know what he’s missing right now. Also, he should find solace in the fact that at 25 years old, he is disease free (I “lost my virginity officially” at 25). You should too.

theKinkKit: Firstly, it seems like you have open communication around sex, which is a *fantastic* place to be. The fact that you are able to get physically intimate is also great. It seems like, right now, he is learning to trust you, and you are doing a great job.

From reading your dilemma, here are the two immediate roadblocks I see that can impact your potential pleasure, and the future of your relationship:

1. While you are being patient and compassionate, you also have sexual needs and don’t want to get sexually frustrated.

2. Not only is he a virgin to penetrative sex, which can be anxiety-inducing in and of itself, but he has an additional mental block resulting from past trauma.

While there are many ways I could approach this topic, especially in regards to overcoming trauma, my suggestions are just going to focus on finding pleasure in alternative ways than just penetrative sex, so that you both can continue to build your sexual compatibility as your relationship and intimacy deepens (because sexual compatibility is so much more than how A fits into B.) 😉

**A) Use toys and get your rocks off, girl! 🙂 Involve him in the process as well.**

Start slow. Ask him if he minds watching you bring yourself to orgasm with your hands (& see if he’s comfortable with mutual masturbation while you do so). Then introduce a small toy (maybe a bullet or egg vibe). Then see if he’s comfortable using the bullet or egg on you. Then try for a g-spot toy, such as the njoy curved Wand (it’s ahhhh-mazing, and has the added benefit of not looking like a penis, which can at first be intimidating and encourage dick-comparisons for boys who aren’t familiar to toys yet ..ie “are you replacing me?//I don’t look like that!”), and use it with a bullet or egg.

Then, if he is comfortable and an enthusiastic participant in all of the above, you may then decide to move up to a dildo of some sort, and seeing whether he would be comfortable restraining your hands (and/or blindfolding you) and penetrating you with a dil. Not only is that: A) really hot, but B) it lets him take control on his own terms, and C) he’ll be “penetrating” you, minus the anxiety of performing. It’s all good ways to gradually introduce him to the idea of penetrative sex with positive reinforcement… and it’s good vibes for you 😉 (plus, if/when you do end up getting to penetrative sex, AND you’ve already played with toys together, if you want to move up to anal sex, having him penetrate you vaginally with a plug or dil already in the booty is *phew*!)

**B) Get kinky with some powerplay/roleplay games that do NOT involve penetrative sex.**

I’m talking Domination/submission powerplay. This may seem like a jump forward, I know… In “traditional”//vanilla dating, kink is quite often practiced *after* penetrative sex — like, long after … when intimacy in the relationship has taken a nosedive and the bedroom practices are getting boring. But hear me out.

The brain is our largest sexual organ; arousal sparks first in the brain, which then sends signals to the body to react accordingly (sending blood to the genitals, producing natural lubrication, etc.). If there is an anxiety, insecurity, or past trauma surrounding a particular sexual act (i.e. penetrative sex), the brain signals will be unable to overcome those roadblocks and send its sexy signals. Therefore, I suggest removing the cause of anxiety by playing some sexy powerplay/roleplay games that do not revolve around sex.

*Why games?*

1) Games incite laughter; laughter is a great way to dispel fear and anxiety and become more present in the moment.

2) Games incite competitiveness. Wanting to “win” or prove oneself can help distract from feelings of fear or anxiety.

**3) Most importantly: Games can automatically create a safe space because you can create rules and set limits within comfort zones.** If you start playing a sexy game, and set a rule like “You are not allowed to penetrate me, no matter how much I beg,” you may both already know that penetrative sex is off the table, but vocalizing it playfully in a rule of a game automatically sets the expectation that this game will be a safe space for him.

4) You can create fake scenarios or roleplays that allow you both to behave like different characters and assume different mindsets. A super easy roleplay would be to give him control and have him give you 3 rules to follow… you are only allowed to address him as “Sir”, and he can give you rules, and if you “break” them on purpose he can give you a playful spanking, etc. You can pretend to beg for penetrative sex and (according to the rule) he can deny you, etc. Or, flip the script: he has to call you “Mistress”, and you are in control… then you tease him, or give him orders on how to please you, etc.

I have a ton more games and ideas for games (I actually started a company specializing in “sexperiential learning”, ie. hands-on sex ed for adults, including sexploration games), but I hope some of those suggestions are helpful, and I wish you both the best of luck and many passionate nights to “come”! 🙂

LukeTheApostate: Not the first in this thread to offer this opinion, but speaking as a male survivor of childhood sexual abuse, his position and reactions are *intensely* familiar to me. Freezing especially. I spent most of my life completely unaware that what I had experienced was abuse; abusers often frame it as “love” or “normal” and kids don’t have the skepticism to investigate that claim. And with no reason to examine those old claims, the adult- me for sure, and possibly your new lad- is unaware that their experience and reactions are abnormal or correctable.

#THERAPY

Get him to consider therapy. CBT techniques work for this sort of thing whether or not he ever becomes aware of his (presumed) trauma- or even if he did not experience trauma and just wants to enjoy sex without anxiety. I do not guarantee that it will work perfectly, but it’s got a pretty good statistical track record. And for unscientific anecdote, after I did (years of) therapy I went from freezing permavirgin to having a deeply enjoyable sex life.

stefencarson: Let him know to tell you when he is ready. If he wants, this can even be a text giving you the heads up. I was a late virgin and that is what me and my gf did. When I was ready, I let her know and we both went to get tested first and shared the results. Then I left it up to her to initiate at a natural time. Zero stress. Worked great.

MaesterTuan: He was raped as child. Might need professional help..

tonyboloney93: I know I’m not offering any advice here but the fact that you’re cool about that says a lot about you. He’s got himself a keeper 🙂